The invention provides a method comprising hydrogenating a ketone in the presence of (i) a base, (ii) hydrogen gas and (iii) a catalyst comprising a charged or neutral complex of formula (I):

##STR00001## wherein: Mn is a manganese atom or a manganese ion in oxidation state (I) to (VII); R.sup.1 and R.sup.2 are each independently optionally substituted C.sub.4-8monocyclic aryl or C.sub.3-7monocyclic heteroaryl moieties; -Fc- denotes a ferrocene (bis(η.sup.5-cyclopentadienyl)iron) moiety covalently bonded via adjacent carbon atoms of one of the two cyclopentadienyl moieties, and which may be optionally further substituted, in either cyclopentadienyl ring; —Z— is an alkylene linker of the formula —(CH.sub.2).sub.1-6— in which one or more of the hydrogen atoms of the alkylene may be independently substituted; —N.sup.x is an optionally substituted nitrogen-containing heteroaryl moiety, with the proviso that at least one of R.sup.1, R.sup.2 and —N.sup.x is substituted one or more times with an electron donating group; and L.sup.1-L.sup.3 constitute one, two or three ligands, wherein, when the complex of formula (I) is charged, the catalyst comprises one or more additional counterions to balance the charge of the complex.

The invention provides a method comprising hydrogenating a ketone in the presence of (i) a base, (ii) hydrogen gas and (iii) a catalyst comprising a charged or neutral complex of formula (I):

##STR00001## wherein: Mn is a manganese atom or a manganese ion in oxidation state (I) to (VII); R.sup.1 and R.sup.2 are each independently optionally substituted C.sub.4-8monocyclic aryl or C.sub.3-7monocyclic heteroaryl moieties; -Fc- denotes a ferrocene (bis(η.sup.5-cyclopentadienyl)iron) moiety covalently bonded via adjacent carbon atoms of one of the two cyclopentadienyl moieties, and which may be optionally further substituted, in either cyclopentadienyl ring; —Z— is an alkylene linker of the formula —(CH.sub.2).sub.1-6— in which one or more of the hydrogen atoms of the alkylene may be independently substituted; —N.sup.x is an optionally substituted nitrogen-containing heteroaryl moiety, with the proviso that at least one of R.sup.1, R.sup.2 and —N.sup.x is substituted one or more times with an electron donating group; and L.sup.1-L.sup.3 constitute one, two or three ligands, wherein, when the complex of formula (I) is charged, the catalyst comprises one or more additional counterions to balance the charge of the complex.

A method for preparing the borate ester using a lithium compound includes: under the inert gas, stirring and mixing carboxylic acid and borane, and a catalyst lithium compound is added, then the borate ester is obtained with hydroboration; wherein the hydroboration is at room temperature for 10 to 80 min. After the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate esters with different substituents. The lithium compounds are n-butyl lithium, lithium aniline, p-methyl lithium aniline, o-methyl lithium aniline, 2-methoxyaniline lithium, 4-methoxyaniline lithium, 2,6-dimethylaniline lithium, and 2,6-diisopropylaniline lithium. The lithium compounds disclosed in the present invention can catalyze the boron hydrogenation reaction of carboxylic acid and borane with high activity under room temperature conditions; the amount of lithium compound is 0.1-0.9% of the molar amount of carboxylic acid.

A method for preparing the borate ester using a lithium compound includes: under the inert gas, stirring and mixing carboxylic acid and borane, and a catalyst lithium compound is added, then the borate ester is obtained with hydroboration; wherein the hydroboration is at room temperature for 10 to 80 min. After the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate esters with different substituents. The lithium compounds are n-butyl lithium, lithium aniline, p-methyl lithium aniline, o-methyl lithium aniline, 2-methoxyaniline lithium, 4-methoxyaniline lithium, 2,6-dimethylaniline lithium, and 2,6-diisopropylaniline lithium. The lithium compounds disclosed in the present invention can catalyze the boron hydrogenation reaction of carboxylic acid and borane with high activity under room temperature conditions; the amount of lithium compound is 0.1-0.9% of the molar amount of carboxylic acid.

Disclosed is a method for preparing a boric acid ester using non-catalyzed hydroboration of a carboxylic acid. The method includes: in an inert gas atmosphere, mixing pinacolborane and a carboxylic acid and stirring until uniform in a reaction flask subjected to dehydration and deoxygenation treatments, reacting for 6-12 hours to obtain the boric acid ester, then adding silica gel and methanol, and conducting a hydrolysis reaction to prepare an alcohol compound. The carboxylic acid is acetic acid, caproic acid, pentanoic acid, heptanoic acid, trimethylacetic acid, adipic acid, benzoic acid, 4-bromobenzoic acid, 4-fluorobenzoic acid, 1-naphthoic acid, 2-methoxybenzoic acid, 4-tert-butylbenzoic acid, 4-ethoxybenzoic acid, 2-bromobenzoic acid, 4-iodobenzoic acid, 3-phenylpropionic acid, diphenyl acetic acid, 2-phenylbutyric acid, indole-3-acetic acid, o-carboxyl phenylacetic acid or 2-methyl-5-bromobenzoic acid. The present invention utilizes a carboxylic acid to efficiently undergo hydroboration with borane without a catalyst for the first time.

Disclosed is a method for preparing a boric acid ester using non-catalyzed hydroboration of a carboxylic acid. The method includes: in an inert gas atmosphere, mixing pinacolborane and a carboxylic acid and stirring until uniform in a reaction flask subjected to dehydration and deoxygenation treatments, reacting for 6-12 hours to obtain the boric acid ester, then adding silica gel and methanol, and conducting a hydrolysis reaction to prepare an alcohol compound. The carboxylic acid is acetic acid, caproic acid, pentanoic acid, heptanoic acid, trimethylacetic acid, adipic acid, benzoic acid, 4-bromobenzoic acid, 4-fluorobenzoic acid, 1-naphthoic acid, 2-methoxybenzoic acid, 4-tert-butylbenzoic acid, 4-ethoxybenzoic acid, 2-bromobenzoic acid, 4-iodobenzoic acid, 3-phenylpropionic acid, diphenyl acetic acid, 2-phenylbutyric acid, indole-3-acetic acid, o-carboxyl phenylacetic acid or 2-methyl-5-bromobenzoic acid. The present invention utilizes a carboxylic acid to efficiently undergo hydroboration with borane without a catalyst for the first time.

Arene-immobilized Ru(II)TsDPEN Noyori-Ikariya catalysts anchored to silica through the coordinated η6-arene are provided. The catalysts efficiently catalyze many reactions, including the asymmetric transfer hydrogenation of ketones to alcohols.

Arene-immobilized Ru(II)TsDPEN Noyori-Ikariya catalysts anchored to silica through the coordinated η6-arene are provided. The catalysts efficiently catalyze many reactions, including the asymmetric transfer hydrogenation of ketones to alcohols.

A porous chiral material of formula [M(L).sub.1.5(A)].sup.+X.sup. wherein M is a metal ion; L is a nitrogen-containing bidentate ligand; A is the anion of mandelic acid or a related acid; and X.sup. is an anion.

A porous chiral material of formula [M(L).sub.1.5(A)].sup.+X.sup. wherein M is a metal ion; L is a nitrogen-containing bidentate ligand; A is the anion of mandelic acid or a related acid; and X.sup. is an anion.